Showing metabocard for PA(16:0/16:0) (BMDB0000674)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:34:44 UTC
Update Date2020-05-21 16:28:42 UTC
BMDB IDBMDB0000674
Secondary Accession Numbers
  • BMDB00674
Metabolite Identification
Common NamePA(16:0/16:0)
DescriptionPA(16:0/16:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dipalmitoyl-3-sn-phosphatidic acidChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphateChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acidChEBI
Dipalmitoyl phosphatidic acidChEBI
PA(32:0)ChEBI
Phosphatidic acid(16:0/16:0)ChEBI
Phosphatidic acid(32:0)ChEBI
1,2-Dipalmitoyl-3-sn-phosphatidateGenerator
Dipalmitoyl phosphatidateGenerator
Phosphatidate(16:0/16:0)Generator
Phosphatidate(32:0)Generator
1,2-Dipalmitoyl-sn-glycero-3-phosphateMeSH
Dipalmitoylphosphatidic acidMeSH
Dipalmitoylphosphatidic acid, (+-)-isomerMeSH
Dipalmitoylphosphatidic acid, (R)-isomerMeSH
Dipalmitoylphosphatidic acid, ammonium saltMeSH
Dipalmitoylphosphatidic acid, calcium saltMeSH
Dipalmitoylphosphatidic acid, sodium saltMeSH
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorateHMDB
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acidHMDB
1,2-Dihexadecanoyl-rac-phosphatidic acidHMDB
1,2-Dipalmitoyl-sn-glycerol 3-phosphateHMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphorateHMDB
Dipalmitoyl-L-a-phosphatidateHMDB
Dipalmitoyl-L-a-phosphatidic acidHMDB
Dipalmitoyl-L-alpha-phosphatidateHMDB
Dipalmitoyl-L-alpha-phosphatidic acidHMDB
DipalmitoylphosphatidateHMDB
L-a-Dipalmitoyl-phosphatidateHMDB
L-a-Dipalmitoyl-phosphatidic acidHMDB
L-a-DipalmitoylphosphatidateHMDB
L-a-Dipalmitoylphosphatidic acidHMDB
L-alpha-Dipalmitoyl-phosphatidateHMDB
L-alpha-Dipalmitoyl-phosphatidic acidHMDB
L-alpha-DipalmitoylphosphatidateHMDB
L-alpha-Dipalmitoylphosphatidic acidHMDB
Chemical FormulaC35H69O8P
Average Molecular Weight648.903
Monoisotopic Molecular Weight648.47300618
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid
Traditional Namedipalmitoyl
CAS Registry Number7091-44-3
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1
InChI KeyPORPENFLTBBHSG-MGBGTMOVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.66ALOGPS
logP11.88ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity178.57 m³·mol⁻¹ChemAxon
Polarizability80.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000674
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022175
KNApSAcK IDNot Available
Chemspider ID393518
KEGG Compound IDC00416
BioCyc IDCPD0-1422
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5644
PubChem Compound446066
PDB IDNot Available
ChEBI ID73246
References
Synthesis ReferenceAndo, Yoshihiro; Oda, Hiroshi; Matsuyoshi, Shigeru; Maekawa, Naoya. Manufacture of phosphatidic acid alkali metal or ammonium salts using phospholipase D. Jpn. Kokai Tokkyo Koho (2001), 8 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phospholipase D2
General function:
Lipid transport and metabolism
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis.
Gene Name:
PLD2
Uniprot ID:
Q0V8L6
Molecular weight:
105766.0
Reactions
PA(16:0/16:0) → PE(16:0/16:0)details
Enzyme Details
2. Diacylglycerol kinase alpha
General function:
Involved in calcium ion binding
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity.
Gene Name:
DGKA
Uniprot ID:
A0JN54
Molecular weight:
82672.0
Reactions
DG(16:0/16:0/0:0) → PA(16:0/16:0)details
DG(16:0/16:0/0:0) + Adenosine triphosphate → PA(16:0/16:0) + ADPdetails
Enzyme Details
3. Lipin 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
LPIN1
Uniprot ID:
E1BPE8
Molecular weight:
102857.0
Reactions
PA(16:0/16:0) + Water → DG(16:0/16:0/0:0) + Hydrogen phosphatedetails
Enzyme Details
4. 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:
AGPAT1
Uniprot ID:
Q95JH2
Molecular weight:
32005.0
Reactions
LPA(16:0/0:0) + Palmityl-CoA → Coenzyme A + PA(16:0/16:0)details
LPA(16:0/0:0) → PA(16:0/16:0)details
Palmityl-CoA + LPA(16:0/0:0) → PA(16:0/16:0) + Coenzyme Adetails
Enzyme Details
5. 1-acyl-sn-glycerol-3-phosphate acyltransferase delta
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone (By similarity). Exhibits high acyl-CoA specificity for polyunsaturated fatty acyl-CoA, especially docosahexaenoyl-CoA (22:6-CoA, DHA-CoA) (By similarity).
Gene Name:
AGPAT4
Uniprot ID:
Q5E9R2
Molecular weight:
43907.0
Reactions
LPA(16:0/0:0) + Palmityl-CoA → PA(16:0/16:0) + Coenzyme Adetails
Enzyme Details
6. Phospholipid phosphatase 2
General function:
Not Available
Specific function:
Magnesium-independent phospholipid phosphatase that catalyzes the dephosphorylation of a variety of glycerolipid and sphingolipid phosphate esters including phosphatidate/PA, lysophosphatidate/LPA, sphingosine 1-phosphate/S1P and ceramide 1-phosphate/C1P. Has no apparent extracellular phosphatase activity and therefore most probably acts intracellularly. Also acts on N-oleoyl ethanolamine phosphate/N-(9Z-octadecenoyl)-ethanolamine phosphate, a potential physiological compound. Through dephosphorylation of these bioactive lipid mediators produces new bioactive compounds and may regulate signal transduction in different cellular processes (By similarity). Indirectly regulates, for instance, cell cycle G1/S phase transition through its phospholipid phosphatase activity (By similarity).
Gene Name:
PLPP2
Uniprot ID:
Q2HJ61
Molecular weight:
32328.0
Reactions
PA(16:0/16:0) → DG(16:0/16:0/0:0) + Hydrogen phosphatedetails